A Founder's Guide on When to Invest in Content Marketing and What to Try First

An investor told you to invest in content marketing. They're not wrong. Content is evergreen and durable.

But you're the founder of an early-stage startup with limited runway. The Catch-22? You're on a ticking clock and need to get going, but you don't have endless resources. You have to ask yourself when you should start.

Investing at the wrong time could sink your business. Too early, and you can run out of cash and miss out on the lower-hanging fruit of other channels. Too late, and your competition leaves you in the dust.

As a founder, I learned that you need to take a couple of steps before investing in content. This is my guide to what to try before diving into content, what content to write, and what to avoid.

First, Start Selling Directly to Your ICP

Before you even start thinking about content marketing, you need to understand your market by talking to prospects and selling directly to them.

Your goal at this stage is to get feedback and talk to as many people as possible, so just get on the phone as often as you can. Do things that don't scale — that means direct sales.

1. Leverage Professional Networks To Get Initial Customers

Why now?: Getting on the phone with people is the cheapest, quickest way to kickstart sales outreach. It takes time and doesn't scale, but you need to start somewhere.

1. First, reach out to potential ICPs in your network. Could you sell your product to any of your friends?
2. Once you've sold to people you know, ask them whether they can make warm introductions to anyone else who would be interested in your product.
3. Next, reach out to people cold via email or DMs on social media channels like LinkedIn or Twitter. A tool like Apollo can do the heavy lifting for you. It gives you access to a huge contact database and can automate email sequences.

‎And if you want responses, you have to make your messaging personal and offer value before you make an ask. Nobody likes generic mass emails.

You need to figure out other ways to make interactions more personal. I'm not talking about yelling "Go Bears!" at a UC Berkeley grad. Talk about how you can solve specific issues they may be facing.

2. Run Retargeting Ads with Your Email Campaigns

Why now?: Once you have your cold email sequences set up, it's time to consider running ads. It's quick and easy to get started. But don't try this if you haven't done step three above — you won't have the volume for it.

Retargeting ads help introduce new leads to your company based on the behavior or persona of prospects who have visited your site before. This is done in two ways:

• Pixel-based retargeting. This involves placing a JavaScript pixel on a visitor's browser during their visit to your site, allowing other sites and social media platforms to display targeted ads based on the viewed pages.
• List-based retargeting. This involves uploading a list of email addresses to a platform like LinkedIn or Facebook, which identifies users with matching emails and delivers personalized ads to them. 

You can create a lookalike audience on LinkedIn and Facebook according to tracking pixels and lists, segment prospects, set your budget, and create ads.

Get Started with Content the Right Way

Once you finish the above steps, let's start dipping our toes into content. But we're not going to dive into hiring an SEO agency. We're going to do this tactfully in an order that makes sense.

1. Build a Following By Participating in Channels Where Your ICP is Active

Why now?: You want to get your name out there and people to recognize you. You should start building a presence on social channels since they're a quick way to push out content and drive short-term results.

First, become active in communities where your ICP lives — LinkedIn, Twitter, Slack communities, Reddit, old internet forums, or in-person meet-ups.

If online, keep these rules in mind:

• Don't just promote yourself.
• Follow and connect with your ICP as well as the thought leaders who your ICPs follow.
• Like and comment on their posts.
• Share your thoughts on the industry, what you're learning, and occasionally share what you're working on with your product.

2. Write Sales Enablement Content Using Customer Conversations

Why now?: Firstly, you'll have something impactful to push out on socials. And second, it helps you move sales conversations forward and can drive revenue immediately.

Any good salesperson knows that selling is more about listening than talking. Gather top questions and insights from early customer conversations to turn into long-form written content.

Here are some great sources for what your customers care about:

• Sales calls: Record them so you can always go back to them. You can do this for free in Zoom.
• Online communities: What are people asking in communities on Reddit or Slack?

We created a guide on how to write your first 20 pieces of content early on and included a helpful framework. Take the information from your initial calls and apply this framework:

• unaware
• problem-aware
• solution-aware
• product-aware

You can share this content with your new-found following from the social media posts in the above step.

3. Use Content in Prospecting Emails

Why now?: Now that you have good content, you can improve your prospecting email sequences from earlier to get responses.

At scale, you can set up automated outbound campaigns segmented into sequences by pain point and include links to your content. At Letterdrop, we have a sequence for prospects with a Webflow site since our CMS brings Webflow to parity with WordPress.

We included a helpful article on adding dynamic tables to Webflow in this email and got a demo booked.

4. Start a Newsletter

Why now?: Now you have some sort of pipeline. You're talking to a bunch of people, and some have probably said no to you or ignored your outreach. Newsletters are a great way to re-engage lost leads and increase the possibility that they will buy from you later.

We recently re-engaged a lead after restarting our bi-weekly newsletter.

‎Think about educating readers on the space, and set up a consistent (and realistic) newsletter schedule.

Remember: a newsletter should be value-additive. It's not a place for shilling yourself.

5. Look for Low-Competition Keywords that Have a High Chance of Conversion

Why now?: You've done the outreach legwork. Some people may come to you because of your social channels, but that's limited. The way you get people to come to you is to finally turn to SEO, focusing your research on low-competition keywords.

But not just any low-competition keywords — ones where you think the searcher has a high chance of converting and booking a demo.

Ignore keywords that are too competitive or too far from your product. For example, if we at Letterdrop typed "content marketing" into Google:

a) Those searchers are not ready to buy our product. They're just getting into content marketing.

b) We're competing with giants like HubSpot and SemRush.

Instead, we know from experience that someone searching for fixes or guides on Webflow, for instance, would consider hopping on a demo call with us. Example pieces we've done on this topic are "Is Webflow Good for SEO?" and "Webflow vs. WordPress."

Some indicators that customers are close to converting include brand searches and searches for alternatives. Writing aggregation and comparison articles is a great way to answer this intent and potentially book a demo.

Next, run ads on your chosen low-volume keywords. See what works and what doesn't.

6. Experiment with Running Ads Against Content

Why now?: You've done a bit of SEO. Now you can start running ads against content.

Content answers informational search intent where ads can't. You'll see conversions and CTR increase while CAC decreases.

We've seen it with Explo, who saw a drop in CPC once they started doing this. They run Google ads on competitive keywords and direct visitors to blog posts that answer search queries.

What Not to Do

Here are some valuable lessons I've learned when it comes to the don'ts of investing in content.

1. Don't hire an agency too early. Agencies are good, but you don't need them at this stage. As a founder, you want to do every job a little bit yourself first so you can really understand the fundamentals before you outsource it to somebody. Agencies work with a lot of companies, and there's a chance they don't fully understand your business. This can be a waste of time and money.
2. Don't start investing in SEO before you've tried other faster channels. SEO can take some time to show results. It's a great long-term channel, but it's not suitable if you want early revenue. After dedicating time to quick-win channels like paid ads and social media, you'll have better-refined messaging and more insights to build a reliable SEO strategy.

There is an exception to the SEO rule, though. If you have a unique opportunity for programmatic SEO, it's worth exploring SEO earlier. Examples include Zillow (location-specific pages), Doordash (business listings), and Zapier (integrations pages.)

Do Some Direct Selling Before Investing in Content

You're on a ticking clock as a founder and don't have much in terms of resources — so it's best to get right into selling before you start investing in content.

Hopefully, this guide helps you kickstart sales and to set up a sustainable content strategy for the long haul.

We help founders get their content ops up and running all the time. In fact, we helped Strac, a data leak prevention platform, drive 80% of their demos with content. Talk to us if you want to start streamlining your content workflow today.